Acetic Anhydride → (4-((5,5-Dimethyl-1,3-dioxan-2-yl)methoxy)-3-methylpyridin-2-yl)methanol

HRID 31568Notes

Reaction equation

HRID 31568 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:7][O:6][CH:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][N+:13]([O-])=[C:12]([CH3:17])[C:11]=2[CH3:18])[O:4][CH2:3]1.C(OC(=O)C)(=[O:22])C.[OH-].[Na+]>>[CH3:1][C:2]1([CH3:19])[CH2:7][O:6][CH:5]([CH2:8][O:9][C:10]2[CH:15]=[CH:14][N:13]=[C:12]([CH2:17][OH:22])[C:11]=2[CH3:18])[O:4][CH2:3]1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 597925544-((5,5-Dimethyl-1,3-dioxan-2-yl)methoxy)-2,3-dimethylpyridine 1-oxide

Product 1

HCID 59792348(4-((5,5-Dimethyl-1,3-dioxan-2-yl)methoxy)-3-methylpyridin-2-yl)methanolYield 39.7%

Conditions

Temperature
85 °C

Procedure

The 4-((5,5-dimethyl-1,3-dioxan-2-yl)methoxy)-2,3-dimethylpyridine1-oxide (3.1 g, 11.6 mmol) obtained by the step (1c) was mixed with acetic anhydride (9.87 ml, 104 mmol). After the mixture was stirred at 85° C. for 45 minutes, acetic anhydride was removed. The residue was dissolved in methanol (40 ml) and a 5N aqueous sodium hydroxide solution (5.1 ml, 25.5 mmol) was added to the mixture while cooling on ice. The mixture was stirred at room temperature for one hour. Methanol was distilled off and ice water was added to the residue, which was then extracted with ethyl acetate. The organic layer was washed with a saturated saline solution, dried over anhydrous magnesium sulfate. After the solvent was distilled off, the resultant mixture was purified by silica gel column chromatography (silica gel: 120 g, elution solvent: ethyl acetate/heptane=1/4 to 4/1) to obtain the title compound (1.23 g, yield: 39.7%) as a light yellow oil.

Workup

  1. customacetic anhydride was removed
  2. dissolutionThe residue was dissolved in methanol (40 ml)
  3. temperaturewhile cooling on ice
  4. stirringThe mixture was stirred at room temperature for one hour
  5. distillationMethanol was distilled off
  6. additionice water was added to the residue, which
  7. extractionwas then extracted with ethyl acetate
  8. washThe organic layer was washed with a saturated saline solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationAfter the solvent was distilled off
  11. customthe resultant mixture was purified by silica gel column chromatography (silica gel: 120 g, elution solvent: ethyl acetate/heptane=1/4 to 4/1)

Sources & evidence

ORD record
ord-094c8d08a4b74733a43992c7acde7dc8
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Reaction notes

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